Water as the reaction medium for multicomponent reactions based on boronic acids

被引：85

作者：

Candeias, Nuno R. ^{[1
]}

Cal, Pedro M. S. D. ^{[1
]}

Andre, Vania ^{[2
]}

Duarte, M. Teresa ^{[2
]}

Veiros, Luis F. ^{[2
]}

Gois, Pedro M. P. ^{[1
]}

机构：

[1] Univ Lisbon, Fac Farm, iMed UL, P-1649003 Lisbon, Portugal

[2] Inst Super Tecn, Dept Engn Quim & Biol, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal

来源：

TETRAHEDRON | 2010年 / 66卷 / 14期

关键词：

Boron; Multicomponent reactions; Petasis reaction; Boron heterocycles; MOLECULAR-ORBITAL METHODS; POLARIZABLE CONTINUUM MODEL; GAUSSIAN-TYPE BASIS; ORGANIC-REACTIONS; EQUILIBRIUM GEOMETRIES; BASIS-SETS; AMINES; ACCELERATION; 2H-CHROMENES;

D O I：

10.1016/j.tet.2010.01.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Water is a suitable medium for the Petasis-borono-Mannich multicomponent reaction Salicylaldehyde, glyoxalic acid, glycoaldehyde and glyoxal were reacted with several boronic acids and different amines affording alkylaminophenols, 2H-chromenes, alpha-amino acids, alpha-amino alcohols and 2-hydroxylmorpholines in good to high yields An efficient new one-pot method for the assembly of boron-heterocycles based on amino-acids, boronic acids and salicylaldehyde using water as the reaction media is presented The mechanisms of these reactions were studied by means of OFF calculations, and the effect of solvent on the calculated energy barriers was addressed, for different aldehydes (C) 2010 Elsevier Ltd All rights reserved

引用

页码：2736 / 2745

页数：10

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